When I asked Amy to our junior prom and she said yes I wasn’t aware that a lot of girls used that event as their steppingstone into womanhood. It was only when I was talking to my brother that he made the comment, about time you got laid. He explained that the prom was a lot more than a dance, it was my chance to finally get my dick wet. He busted my balls all weekend about it and all it did was make me nervous, I was as much a virgin as Amy was. Now I would sweat bullets every time I seen her. Why was high school so complicated?

In a school of over three hundred students I had few friends but I trusted all of them with my life. A couple were best friends and I had to talk to someone about what was coming up. His name is Jimmy and we’ve known each other since we were born. I told him what my brother said and he said it was all true. Girls had this thing about losing their virginity at proms and I was one lucky bastard, Amy was smoking hot. That I agreed with, Amy was so pretty and had a cute little body. Sometimes I would watch her walking away and just staring at her ass would get me hard. None of that helped me though, I was still the kid with zero experience and was going to make a fool out of myself in front of her. I needed his help to tell me what I should do to get ready for her.

“Ross don’t let it get you paranoid. She is just as in the dark in what to do as you are. Just let it happen, just don’t shoot your load to soon and make a mess of her (Laughing). Seriously though if you’re that worried do something about it. Remember what Jack said about Melody. He said she put out just because he kissed her. Take a shot with her first, let her show you a thing or two- and that-way Amy might see you as someone that knows his shit. Worst case scenario, you get fucked by the ugliest girl in school, but you still get laid. The risk is Amy finding out what you did and thinks you’re a creep. Either that or find someone else you can try things with in private, that won’t spill the beans”.

He was right, but I don’t know if Melody was the answer. She has a big mouth and if anyone finds out I had sex with her I would have everyone riding my ass about it, including Amy. No, I needed to find someone that wouldn’t say a word. someone I trusted more than any other girl, but who?

The dance was in two weeks and I was running out of time. I was sitting on the deck out back when my sister Vicki and her friend Katie came out. Vicki was my twin sister and for a sister she was okay. We still did a lot of things together and until last year when she “grew out of it”, we could talk to each other about anything. I considered asking her what a girl would expect but realized she might be ready to do the same thing, we were in the same grade and going to the same prom. It made me cautious in the things I said now. her friend Katie, a chatter box, seemed to have a thing for me but the feeling was never mutual. Just something about her rubbed me the wrong way from the day we met.

She asked me if I was going to the prom and I said I was. I knew she would be going with Tyler, he was her boyfriend, well for this month anyway. Katie didn’t say a word and I knew nobody asked her. She was just one of those girls that didn’t fit it the way everyone else did. Katie was shy, a little timid, and got nervous around crowds. I didn’t want to embarrass her so I changed the subject but Vicki was as much a ball buster as our brother was and she started to needle me about what I was going to do after the dance. She winked at me and said back of the limo or motel. I should have came back with a remark of my own but I could see Katie withdrawing from the conversation so I chose to just get up and leave.

That night there was a knock on my bedroom door. It was Vicki and she asked if we could talk. She sat on my bed and I sat up and she looked a little frazzled. She said she wanted some advice and I was the only person she trusted, other than Katie but she wasn’t going to be of any help. Now I was intrigued with her sudden need for her twin brother’s time and ear. I told her we could still talk about anything and could still relay on the other to keep it quiet.

“Ross I know what the prom means to a lot of us but for me it is a lot more difficult. I heard through friends that Tyler wants us to have sex that night. Ross, I’ve never had sex, well not in the way you think it. This is hard for me to say so do me a favor and just let me say it all before you make fun of me, I need to tell someone before I burst.

I am and I’m not a virgin. I mean I have never done that but I have done other things. If Tyler is expecting me to let him fuck me I’m not sure I can. I want to, and if he pushes me I probably will, but not for the right reasons. My experiences are all in caressing and oral. Ross, would I be wrong to tell Tyler no, that I’m not ready to have sex completely? I don’t even know if I can give him head if that was an alternative. Ross, please keep this between us. My experiences in sexual arousal have only been with one person and I do enjoy it a lot. The problem is it has been with Katie. For obvious reasons we can’t fuck or I would have with her already. We wanted to go to the prom together but that means revealing who we are and her parents and family would never accept it, ours either, but I can’t be sure.

Now you know, your sister is a lesbian and I am counting on you to keep that our secret. My question is what do I do about Tyler? I want him to be happy, I do genuinely like him and I would do stuff for that reason and to keep my appearance safe from others finding out the truth. I just don’t know what to do, I never had any feeling for a boy that way. what if I do something wrong and he starts spreading rumors about me and I become an outcast? Help me Ross. Help me understand what he would expect me to do, what you think Amy expects you to do and make her feel”.

WOW, that I did not see coming. My sister likes girls. My sister has sex with Katie. WOW, this was a lot to absorb. I cleared my head and thought about the bigger questions. Unfortunately I was pretty much in the same boat. I told her my position and was honest about everything, even Jimmy’s suggestion to find Melody. I told her I was just as nervous in how Amy would see me if I failed to do what I should know. We sat in silence for a few minutes and finally I asked her how bad she needed to know things about having sex with a boy. She said really bad and I looked around as if someone could be listening. I made her a proposition, one that made the hair on my arms stand on end.

“Vicki, we both have identical problems, fear of failure in bed for the first time. You have a little advantage because you did things with Katie. You know what she likes and she knows what you like, I can’t say that about anyone. What if we learned from each other? What if on prom night neither of us had to lose our virginity but instead know what we should be doing? This way Tyler gets what he wants and he’s happy. Amy gets what she expects from me without disappointment so she’s happy, and your secret with Katie is safe so you’re happy. As for me, not looking like an idiot could lead to me having more sex with Amy and since I know you like girls now even you have to admit she has something special going on under her clothes.

I say we have sex together and figure out what is good and what is bad. Learn by listening to each other and following direction that if favorable to the other. It sounds nasty and is about as wrong as it gets but what choice do we have. Vicki, what do you think, should we teach each other how to fuck? Would it be such a horrible thing if you told me what feels good and I show you how I want it done to me? We only have two weeks before the prom, if we’re going to do something we have to decide now. We have always trusted each other, no reason to stop now”.

I waited to see what she thought. I never thought of her that way before, even when I walked in on her changing I never looked, had no reason to. This was what I needed though, someone that I knew wouldn’t tell anyone. This is how I could get myself ready for Amy. Her wheels were spinning and not saying anything in this case was a good sign. If she was grossed out she would have said something right away. I said my peace and now I waited to hear what she thought of the idea.

“Ross I get it; we can trust each other. I know that just by you being able to ask me such a crazy thing. It sounds like a solution to both out problems but I don’t know if I can have sex with my brother, twin or otherwise. It’s a little creepy to think about. There is another way but you might not like it. What if I could watch you having sex? I could still see what I needed to know and there is someone that would let you if you asked. She has liked you a lot since you met. What if I was in the room when you and Katie had sex? We both learn what we need to and Katie gets to finally know what it feels like for a boy to touch her. Ross she has told me as much as she wants to be with me she still wants the experience of losing her virginity with a boy. She wants to know what it feels like to be fucked so why not with you, a boy she already wants in some ways. What do you think”?

I thought about it. Katie was cute and nothing like Melody. She did like me so I think she would say yes even knowing the reason why. Then I had another thought, one that blew my mind. What if one stipulation was either before, during, or after sex, Vicki and Katie had to show me what they like doing to each other? Watching my sister lick a pussy sounded fun. I still wasn’t sure but I had to do something so I suggested we think about it for a day but for tonight I wanted her to let me see her and at least touch her. I would let her do the same but nothing more. she said that would be okay as long as I didn’t tell anyone, especially Jimmy, he had the biggest mouth in school.

I locked my bedroom door and Vicki took her shirt off. She had nice round tits, not super big, but not little bumps either. She kept her bra on and as she took her jeans off I took off mine. She kept her panties on but I dropped my boxers, I wanted her to touch me not my shorts. I was hard as a rock by that time and her eyes couldn’t tear away from me. she was the first to grab and I was right behind her. I loved how soft her tits were once I got under her bra and when she squeezed my dick I cum in her hand. I was so embarrassed as she felt me coating her fingers but she didn’t let go. Vicki said she expected me to do that because it was my first time being touched. Vicki went to clean her hands after I finished and when she came back I took her panties off. She had a pretty pussy with only a little hair growing in. I played with her and she said Katie liked to finger her there so I did that and she was so hot inside. I asked if I could suck her tits and she said no, this was as far as it goes so I made the best of it and squeezed her tits and fingered her pussy until she had an orgasm. That was enough she said, tomorrow we decide what we need to do next.

I had dreams of fucking my sister that night. I knew what her body looked like and how it felt, I liked it all. Tomorrow we decide what comes next but I think I knew all along. I would ask Katie if I could fuck her but knowing she would say yes so easy I wondered if I should ask for more like experiencing my first blowjob. I don’t know if it’s true or not but I heard girls hate it when you cum in their mouth so what does a guy do when he has to release? Is than when I fuck her? Anyway my dream was hot and my sister was an amazing first fuck. Right now she thinks the idea is creepy but who knows what tomorrow will bring. I slept like a rock and with a hard dick all night.

It was Saturday so no school and dad was working all day. Mom went out to run errands and my brother never even came home last night. After mom left I went upstairs and opened my sister’s bedroom door. She was still sleeping and went to bed naked. I pulled the sheet down to look at her and she had a nice cushion in the back. I thought about waking her up with a slap just for fun but something in me said not to, to wake her up a different way. I leaned down and kissed her ass cheek. I thought I would get a laugh out of it from me and from her but she didn’t even budge so I kissed it again, and again, and again. Nothing and what started as a joke was becoming just a little bit more and I grabbed her cheeks with both hands and pulled them apart. I wanted to see her pussy again but what I seen was her tiny poop hole. Something about it made me curious, something I either read or seen online.

With her cheeks apart I leaned in and kissed her again, this time avoiding her cheek and kissing her tiny hole. Vicki could sleep through anything so maybe she needed me to tickle her to wake her up. I wanted us to figure out this whole Katie deal early. I stuck out my tongue and closed my eyes not wanting to see what I was doing and I licked her hole. I felt her body tense up and then relax. I felt her legs open a little more than before, and when I put my tongue back she let out the cutest little sigh. This I found strange considering what I was doing. She turned her head to see my face planted in her butt crack and all she could say is I thought you didn’t know anything.

I stopped and she rolled over. Vicki said that was something a girl either loved or hated so not to do it unless I was sure. Then she hit me with her pillow and said I told you nothing else. She got up to get dressed and I stared at her naked body. My sister was making me hard again. I took it out and asked if she would try again, this time I promised not to be done as fast. She took it in her hand and it felt just as good and I told her I can’t, I was going to cum again only this time she was able to grab something from the floor and I cum in her panties from last night. Vicki said the way I felt was amazing in her hand. She held me tight and I motioned her to stroke it. She did and just like that I started to cum a second time. fuck, my sister was turning me on way too much.

With mom out and dad working Vicki called Katie and had her come over. she said she had no secrets with her so they could ask her together. I told her what other thing I wanted and she called me a pig. Turns out she was joking and said they might be willing to show me some things but I would owe both her and Katie something down the road. We shook on it and when Katie came over we all went in Vicki’s bedroom where I told her I wanted to experiment with sex and wanted her to explore it with me. she looked at Vicki who was nodding her head in approval and Katie said she would but only if I promised not to cum in her, she didn’t want to risk getting pregnant. She asked when and I though now was as good a time as any and even suggested she does things with Vicki first so her body was aroused and wanted more. she turned and gave me a kiss and then gave Vicki an even bigger one.

I watched my sister and her girlfriend playing with each other. I watched them sucking tits and rubbing pussies. It was so hot I took my pants off and jerked off to them. They knew I was there and knew what I was doing and I think it made it better for them. When Vicki opened Katie’s legs I was invited to watch her eat her pussy and learn where and how. Katie was about the same as Vicki except her pussy lips were bigger and her tits were definitely bigger. She let me try a few times and I loved how it felt. While Vicki was doing her girlfriend I went to ask if she would put my dick in her mouth. She said she would rather not but I could rub it on her tits so that’s what I did.

After that they both took turns stroking me and watching how hard I got. I was grateful with two girls playing with me I didn’t make a mess of both of them. I reached down and could play with Katie’s pussy but when I tried to play with Vicki she pushed me away and reminded me I wasn’t allowed to do that. I ate Katie’s pussy on my own and she said I made her cum but I needed to be more attentive to the little things like feeling how she reacted to me touching her in the good places. She guided me and stopped me when it felt the best. Vicki watched us from the end of the bed and said she liked this and said I needed to start fucking. I asked Katie if she was sure and she kissed me and said, fuck me Ross, be the first one but remember, don’t ever cum in me.

Vicki was as excited as I was and even held her girlfriends legs up and open for me. I started to fuck her and felt something stopping me. Katie told me push harder, it would give way and it did. She yelled that it hurt but Vicki said for me to keep going. Everything was so hot and so tight around me. The deeper I went in the more Katie screamed out but I didn’t stop. This was the best thing ever and my sister never took her eyes off me fucking her girlfriend. After a minute her natural juices took over and fucking felt incredible. To incredible as now I had to cum so bad and when I took it out I grabbed Vicki’s hand and said make me cum sis. She stroked me five or six times and I blew a gasket. Vicki wasn’t thinking ahead, or was she, and I cum all over Katie’s stomach and tits. watching Vicki and where she made me go was fucking awesome. Katie said she loved watching my cum flying out of me and it was better I did it on her and not in her. Vicki asked Katie what it was like to get fucked and she said it was something she had to know, she had to try.

Katie was so excited she was no longer a virgin her and my sister did a sixty-nine in front of me. this was just as good to watch as I could play and they were so preoccupied it didn’t matter. I finger fucked both of them, while Katie licked my sister’s pussy I went behind her and licked her asshole again. She said two tongues made her cum instantly. When I tried to do the same to Katie she squirmed and wiggled as her way of saying don’t do that so I stopped. Vicki did say some like it while others don’t.

That entire morning was spent on me discovering Katie’s body. Even with my sister looking on and us telling each other what we were feeling I knew there was something else I wanted. She would say no but I wanted to fuck my sister next. Katie let me fuck her three times that day. By the third I was able to control my stream and not be so quick. Katie took the first two on her tits but the third I manipulated how we were and asked my sister to lick Katie’s pussy while I was in her. She did and Katie was in heaven. When I was ready I pulled out at the last second and started to cum. It took her a second to realize what was happening but I managed to cum in my sister’s mouth. She jumped up and I watched her reactions carefully. She said she was disgusted but I didn’t see anything dripping from her mouth. My sister swallowed my cum and she can say what she wants but I know she liked it. Vicki might be a lesbian but she still has a curiosity she couldn’t fight. Katie watched it all unfold and after seeing what I did and how Vicki reacted she told me next time she might let me put it in her mouth just to see what it was like. Katie then kissed Vicki and in her amusing way said she wanted to see if she could still taste cum on her tongue.

Things went on like that for a week. Katie spent a lot of nights at our house and would come to my room when everyone was asleep. Sometimes alone, sometimes with Vicki. Vicki still insisted I not have sex with her, that touching was enough but when her and Katie went at it and I took my mouth and catered to her fun little hole she never refused me. I still wanted to fuck her and I tried a bunch of times but she kept saying no. I was getting better and Katie was beginning to do more with me like suck my dick and twice I cum in her mouth. The first time she spit it out, the second time right after I filled her mouth she kissed my sister and I knew they were sharing it. I know the next time she would take it and swallow with no hesitation. Yup, Katie was worth the effort, she was a dynamite piece of ass and the more we got together, the less I thought about Amy. The more time I spent with my sister, the more I knew us having sex was going to happen.

With only five days until the prom I woke up to the feel of Vicki slipping in my bed. She said she tried as hard as she could not to want this to happen but she didn’t want Tyler to think she was inexperienced if things went that far. She said for me not to think of it as anything more than a brother helping his sister out of a difficult position. Vicki rubbed against me and I knew she was naked. She turned to whisper to me that she wanted me to be the first. She grabbed my dick and said she wanted to lose her virginity to someone that she could trust not to think she was a slut or talk about her. Vicki asked me to fuck her.